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HCID 17851043, Verbindung → HCID 54030461, Verbindung

HRID 1765985
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1765985
[C:1]([NH:4][CH:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=1)(=[O:3])[CH3:2]>O.[OH-].[Na+].[Co](Cl)Cl>[C:1]([NH:4][C@@H:5]([C:16]([OH:18])=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 17851043HCID 17851043, Verbindung

Produkt 1

HCID 54030461HCID 54030461, VerbindungAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24288Cobalt(II) chlorideKatalysator2×HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

In a mixture of water (36.5 ml) and 1N sodium hydroxide solution (29 ml) was dissolved N-acetyl-3-methoxy-4-methyl-DL-phenylalanine (7.28 g). Cobalt chloride (II) hexahydrate (36.5 mg) and acylase (Acylase Amano 36.5 mg) were added to the solution and the mixture was stirred at 37° C. for 15.5 hours while adjusting pH of the reaction mixture to 7.5 with 1N sodium hydroxide solution. Insoluble matters were removed by filtration and pH of the filtrate was adjusted to 3 with 6N hydrochloric acid. After extraction with ethyl acetate, the extract was washed with water, dried over sodium sulfate and the solvent was evaporated under vacuum to give crude N-acetyl-3-methoxy-4-methyl-D-phenylalanine (3.17 g). The crude product was subjected again to the acylase reaction (15.2 mg cobalt chloride (II) hexahydrate, 152 mg acylase, 37° C., pH 7.5, 20 hours) to give pure N-acetyl-3-methoxy-4-methyl-D-phenylalanine (2.70 g) in the form of a viscous oily substance.

Aufarbeitung

  1. customInsoluble matters were removed by filtration and pH of the filtrate
  2. extractionAfter extraction with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customto give crude N-acetyl-3-methoxy-4-methyl-D-phenylalanine (3.17 g)

Quellen und Nachweise

ORD-Eintrag
ord-29ce840310b54b7aa04277168bdd53ea
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07229992B2

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